Coloring pelts, furs, hairs, feathers, and products manufactured from these materials



Patented Oct. 5, 1937 PATENT OFFICE I COLORING PELTS, FURS, HAIRS,FEATHERS, AND PRODUCTS MANUFACTURED FROM THESE MATERIALS Erich Lehmann,Priorau, Kreis Bitterfeld, Germany, assignor to General Aniline Works,Inc., New York, N. Y., a corporation of Delaware No Drawing. ApplicationMarch 3, 1937, Serial No. 128,870. In Czechoslovakia July 4, 1934 28Claims.

The present invention relates to a new process for dyeing pelts, furs,hairs, feathers and products manufactured of these materials, such as,for instance, hair-felts. More particularly it relates to such a processin which the dyeings are produced with the aid of several dyeingsubstances.

A known mode of dyeing pelts and similar materials various tints fromyellow to black consists in bringing the pelt in suitably preparedcondi- 1 tion into a. bath which contains, besides a suitable oxidizingagent, a mixture of certain aromatic diamines and/or aromatic hydroxycompounds or of suitable substitution products of 5 these substances.These dyeing agents are used, for instance, in form of free bases, assalts of inorganic acids in a neutral dyeing bath, or with addition ofammonia; hydroxy compounds, often, are employed together with causticalkalies. 20 When preparing the dye baths, the specific chemicalbehavior of the difierent pelt dyes of this kind is to be regarded.Thus, for instance, the hardness of the water plays an essential part ifthe bath is set with salts of aromatic amines with an 25 inorganic acid.Furthermore, the possibility of shading the final tints by addition ofother fur dyes is limited inasmuch as in many cases not the sum of theindividual tints of the components is exhibited, but a reaction betweenthe 30 dye components causes an undesired shading. In

this connection it may be mentioned that a mixture of certainmeta-diamines and para-diamines produces when dyed on pelts in the usualmanner blue-colored indamines which are comparatively 35 unstable andeasily change to another color, generally red, for instance, when thepelt is hotironed or during storage. Moreover, such oxidation dyes giveundesirably dark-colored fleshsides. In consequence of their freetendency to react with other dyes suitable for pelts, a shading towardsblue can be obtained only exceptionally with the aid of these dyes.

Mixtures of known dyes suitablefor pelts and 45 dyeings producedtherewith'often sublime and droxynaphthalene,1.5-dihydroxy-2-aminonaphare not stable in store. Moreover, in solutionsof flie'mixtures, in consequence of the diflering solubility of thecomponents, there occur variations in the concentration of the dye-bathwhich interfere with uniform dyeing, so that it becomes 5 difiicult forthe dyer to obtain in every case the same tint and color strength.

All these defects are reduced to a minimum and uniform, very beautifuland stable dyeings 10 are obtainable when using in the dyeing operationa salt-like compound or mixture of such compounds which is formed ofpolyhydroxy compounds of the benzene series, a hydroxy-, aminohydroxy-,halogenohydroxy-, halogenohydroxyamino compound of the naphthaleneseries, which may be substituted by an inert group such as alkyl, alkoxyand aralkyl and from an aromatic base. These salts exhibit, besidestheir good stability in store, a remarkable aflinity to hair, so thatthe flesh side of the pelt is to some extent reserved from the dye andthey dissolve in water in such a. manner that the dye bath alwayscontains the salt components in the desired ratio. There is thecertainty that the dyer will obtain in every case the same tint andcolor strength.

-As acid constituent of the said salts there may be enumerated: 1.2-,1.3-, 1.4-dihydroxybenzene, 1.2-, 13-, 1.5-, 1.6-, 1.7-, 1.8-, 2.6-, or2.7- dihydroxynaphthalene, 4-ch1oro-1-hydr'oxynaphthalene,2.4-dichloro-l-hydroxynaphthalene, 1.6-

dihydroxy- 5 -nltronaphthalene, 1 -amino- 5 -hythalene, 2 amino '7hydroxynaphthalene, 1- amino- 8 -hydroxynaphthalene, 1' -amino- 5-hydroxy-8-chloronaphthalene.

The basic substituent of the salts is an amine of the aromatic orheterocyclic series or a derivative or substitution product thereof. Ienumerate, for instance: 13- or 1.4-diaminobenzene, as well as thechloroand nitro substitution products thereof, N-monoor dialkyloraralkyl-substituted derivatives of the 1.3- and 1.4-diamlnothalene,benzidine, 2-aminobenzidine, dianisidine,

and their derivatives substituted in the amino group or in the nucleus.From the heterocyclic series I enumerate: 8-aminoquinoline,8-aminoquinaldine, 5.8-diaminoquinoline' and 3-aminocarbazole. From theacid" constituents, enumerated above, those hydroxy compounds beingsubstituted by an amino group, may act as basic constituent incombination with an acid hydroxy compound.

The salt-like addition products used as pelt dyes according to myinvention, are readily prepared in the manner described in OrganischeMolekulverbindungen by Paul Pfeifler, 2nd Edition, page 270-271, orLiebigs Annalen,

Vol. 438, page '74 et seq., by dissolving the amine,

and the hydroxy compound in equimolecular proportions in an appropriatesolvent, mixing the solution and, if necessary, eliminating the solvent.

The salt-like compounds of this kind dye mordanted or unmordantedmaterials, such as pelts, in conjunction with an oxidizing agent,diiferent shades, whereat in the most cases the flesh side is lessstrongly colored than the hair side. The tints produced are fast toironing and mostly very fast to the action of light. Brown tints areobtainable which are distinguished by their excellent fastness to light,to rubbing, transpiration and sublimation. Furthermore, the salts inquestion do not react with known oxidation dyes, but may be shaded withthem. By combining blue and brown dyeing salts, black tints areobtainable showing an excellent, fastness; while the hair side iscolored deeply black, the flesh side is blue.

If the said compounds used as oxidation dyes,

'are only sparingly soluble in water, the necessary degree of dispersionof the dye in preparing the dye bath, is obtained by addition of asubstance having capillary activity. This is especially recommendablewhen use is made of a highly concentrated dye bath for deep tones. Assubstances having capillary activity there may be used nearly allwetting agents and emulsifying agents described in the relativeliterature. For example, Turkey red oil or highly sulfonated products ofthis kind; sulfonated aliphatic hydrocarbons from brown coal-tar, forexample, sulfonated solar oil; water soluble condensation products ofunsaturated fatty acids with sulfonic acids of aromatic oxy compounds(compare German Specification No. 538,762); sulfonatedalkylnaphthalenes, aliphatic alcohol sulfonates or the like.

If the salts or the mixtures of pelt dyes are wetted only withdifliculty, the wetting character of the added substance may be enhancedwith the assistance of a small proportion of an organic solvent, so thatin all cases there is obtained a sufiicient degree of dispersion of thenew oxidation dyes, accessible for use as may. be needed in also ofvalue in that the hair is thereby made still more receptive of the dyeand the reserving of the flesh side is still further improved.

The present application is a continuation-inpart of my applicationsSerial Nos. 741,873 and 741,877, filed August 28, 1934.

The following examples illustrate the invention, the parts being byweight:-

Example 1.2 parts of the salt made from 1.5- dihydroxynaphthalene and 4aminodiphenylamine are dissolved in 1000 parts of water and the solutionis mixed with 20 parts of hydrogen peroxide solution of 3 per cent.strength. An ironsalt mordanted, white rabbit's skin dyed in this bathfor 3 hours produced a black-blue hair and a full blue flesh side.

Example 2.2 partsof the salt made from 1.5- dihydroxynaphthalene and4-methoxy-4'-aminodiphenylamine are dissolved in 1000 parts of water andthe solution is mixed with 20 parts of hydrogen peroxide solution of 3per cent. strength, A chromium salt mordanted lambskin dyed in this bathfor 3 hours produced a black-blue hair and a full blue flesh side.

Example 3.2 parts of the salt made from 1.6+

dihydroxynaphthalene and 4-methyl-3-aminodiphenylamine are dissolved in1000 parts of water, and the solution is mixed with 20 parts of hydrogenperoxide of 3 per cent. strength. A chromium mordanted lambskin dyed inthis bath for 3 hours is dyed olive-brown tints.

Example 4.--1 part of the salt of 1.5-dihydroxynaphthalene with8-aminoquinoline is dissolved in 1000 parts of water and the solution ismixed with 10 parts of a hydrogen peroxide solution of 3 per cent.strength. A white rabbit's skin mordanted with a chromium salt and dyedin this bath for 3 hours has a deep wine red hair and a light red fleshside.

Example 5.1 part of the salt of 2.7-dihydroxynaphthalene withpara-aminodimethylaniline is dissolved in 1000 parts of water and to thesolution are added 10 parts of a hydrogen peroxide solution of 3 percent. strength. A white rabbit's skin mordanted with an iron salt anddyed for 3 hours in this bath exhibits a full moleskin gray.

Example 6.1 part of the salt of 2.6-dihydroxynaphthalene withpara-aminodimethylaniline is dissolved in 1000 parts of water and to thesolution are added 10 parts of a hydrogen peroxide solution of 3 percent. strength. A white rabbit's skin mordanted with a chromium salt anddyed for 3 hours in this bath exhibitsa deep green hair and a light bluegreen flesh side.

Example ?.-1 part of the salt of 4-chloro-1- hydroxynaphthalene and4-aminodiphenylamine is dissolved in 1000 parts of water and to thesolution are added 10 parts of a hydrogen peroxide solution of 3 percent. strength. A white rabbits skin mordanted with a chromium salt anddyed for 5 hours in this bath exhibits a deep blue hair.

Example 8.1 part of the salt of 2.4-dichlorol-hydroxynaphthalene with1.4-diaminobenzene is dissolved in 1000 parts of water, and to thesolution are added 10 parts of a hydrogen peroxide solution of 3 percent. strength. A white rabbit's skin mordanted with a chromium salt anddyed for 5 hours in this bath exhibits a violet hair.

In a similar way the salts enumerated in the following table aresuitable to be dyed, whereby tints, like'wis'e indicated in this table,are obtainable.

water and. the solution is mixed with 20 parts of a hydrogen peroxidesolution of 3 per cent.

2.4-6 inobenzene. 1.5-dil1 droxynaphthaleno and l-methoxy 2.4-deminobenzene.

Violet brown 1.6-dihydroxynephtbelene and i-nitro-2- Clear yellowYellowish beige.

dimcthylamino-li-eminobenzene. brown.

LB-dihydroxyna htbalene and 1.4-diam- Dark brown..

ino-2-dimethy amino-benzene.

1.6-dihydroxynaphthalene and 4-emino- Bluish green 4'-dimethylaminodihenylamlne.

Lab-gill (groxynaphth one and Z-amino- Full red brown-..- Beige.

nz ne.

Lb-dihydroxynephthalene and a-emimr Reddisli grey cerbezole.

Lil-dihydroxynephthalene and l-chloro- Black brown.

Z-monomethylamino-lS-eminobenzene.

LB-dihydroxynephthelene and l-nitro-2- Yellow olivedimethylamino-4-emlnobenzeue.

l.6-dihydroxynaphthalene and 1.5-naph- Black brown thylendiamine.

1.6-dihydroxynaphthalene and 2.6-diam- Tobacco brown...

inonaphthalene.

2.6-dihydroxynaphthalene and l-nitro- Olive brown Greenish yellow.

2.4-diaminobenzene.

2.7-dihydroxynaphthalene and 1.5-naph- Reddish brown.--

'thylendiemine.

1.6dihydroxynaphthalene and l-amino- Dark brown Beige.

b-hydroxynaphthalene. I

l.5-dihydroxy-2-aminonaphthalene and Violet brown Reddish brown.

lA-dieminobenzene.

l-amino-fi-hydroxynaphthalene and 1.4- Deepiy blue Red'dish blue.

diaminobenzene.

l-hydroxy-8-aminonaphthalene and 1.3- Brown dlaminobenzene.

2-hydroxy-7-aminonaphthalone and 4.4] Greenish blue..." Greenish blue.

diaminodiphenyiamine. 4

As mentioned above, the dyeing capacity of the oxidation dyes inquestion can be further improved by adding a dispersing agent to the dyebath. This is shown in the following examples.

Example 9.-2 parts of a mixture of 40 parts of the salt from1.5-dihydroxynaphthalene and 4- amino-4'-dimethylaminodiphenylamine and60 parts of a wetting agent, made as described in German SpecificationNo. 436,881 by condensation of a naphthalene sulfonic acid withbenzylchloride, are together dissolved in 1000 parts of water and thesolution is mixed with 20 parts of a hydrogen peroxide solution of 3 percent. strength. A chromium mordanted white lambskin dyed for 3 hours inthis bath at C. ex-

hibits a black-green hair side.

Example 10.-2 parts of a mixture consisting of parts of the salt from2.7-dihydroxynaphthalene and 4-aminodimethylaminobenzene with 60 partsof Turkey red oil are dissolved in 1000 parts or water and the solutionis mixed with 20 parts of a hydrogen peroxide solution of 3 per cent.strength. In the course of 3 hours a white rabbit's skin mordanted withiron salt is dyed in this bath at 28 C. a full moleskin gray.

Example 11 ..-2 parts of a mixture consisting of 40 parts of the saltfrom 1.5-dihydroxynaphthalene and 4-aminodimethylaminobenzene; and 60parts of an isppropylnaphthalene suli'onic acid are dissolved in 1000parts of water and the solu-' tion is mixed with 20 parts of hydrogenperoxide solution of 3 per cent. strength. In the course of 3 hours awhite lambskin mordanted with alum is dyed in this bath at 28 C.blue-gray.

Example 12.2 parts of a mixture consisting of 40 parts of a salt from2.6-dihydroxynaphthalene and 4-aminodimethylaminobenzene and 60 parts ofan emulsifying agent, made by treating caster oil withl-naphthyl-S-sulfonic acid in presence of strength. When dyed in'thisbath for 4 hours at 32 C. a white rabbit's skin, previously mordantedwith a chromium salt, exhibits a deep green hair side.

Example 13.-2 parts of a mixture consisting of 40 parts of a salt from2.7-dihydroxynaphthalene and 2.4-diaminomethylbenzene and 60 parts ofTurkey redoil are dissolved in 1000 parts .of water and the solution ismixed with 20 parts of a hydrogen peroxide solution of 3 per cent.strength. In this bath, at 30 C., a white lambskin mordanted with aohromiumsalt is dyed in the course of 3 hours a bluish-brown.

Example 14.-40 parts of the salt from 1.5- dihydroxynaphthalene and4-aminodiphenyiamine are mixed with 60 parts of a wetting agent madefrom solar oil (brown coal-tar oil) and xylene in the presence of fumingsulfuric acid as described in German Specification No. 552,328, Example4. 2 parts of this mixture, together withl part of the salt from2.6-dihydroxynaphthalene and 4-aminodimethylaminobenzene are dissolvedin 1000 parts of water and the solution is mixed with parts of ahydrogen peroxide solution of 3 per cent. strength. In the course of 5hours a white lambskin mordanted with a chromium salt is dyed in thisbath at 32 C. a full blue-black with a blue flesh side.

Example 15.-2 parts of a mixture consisting of 40 parts of the salt from1 .2-dihydroxybenzene and 1.4-diaminobenzene and 60 parts of Turkey redoil are dissolved in 1000 parts of water-and 20 parts of hydrogenperoxide of 3 per cent. strength are added to the solution. A whiterabbits skin, mordanted with chromium salt, is dyed in this bath at 30C. a moleskin gray in the course of 3 hours.

Example 16.2 parts of a mixture consisting of 40 parts of the salt from1.3-dihydroxybenzene and 4-aminodiphenylamine and 60 parts ofisopropylnaphthalene sulfonic acid are dissolved in 1000 parts of waterand 20 parts of hydrogen peroxide of 3 per cent. strength are added tothe solution; A rabbit's skin mordanted with a chromium salt is dyed inthis bath, at 30 C., a greenish deep-gray in the course of 3 hours.

Example 17.2 parts of a mixture consisting of 40 parts of the salt from1.4-dihydroxybenzene and 2-chloro-L4-diaminobenzene and 60 parts of awetting agent, made as described in German Specification No. 436,881(compare Example 1) are dissolved in 1000 parts of water and 20 parts ofa hydrogen peroxide solution of 3 per cent. strength are added. A whiterabbit's skin, mordanted with-a copper salt is dyed in this bath at 30C. a brown in the course of 3 hours.

Example 18.A mixture of 1.6 parts of the salt from1.5-dihydroxynaphthalene and 4- aminodiphenylamine with 0.4 part of thesalt from 1.3-dihydroxybenzene and 2-chloro-L4-diaminobenzene and with 3parts of a wetting agent, made as described in German Specification No.436,881, is dissolved in 1000 parts of water and the solution is mixedwith 20 parts of hydrogen peroxide solution of 3 per cent. strength. Awhite rabbits skin, mordanted with a chromium salt, is dyed in this bathat 30 C. a full black with a blue flesh side in the course of 3 hours.

Example 19.'2 parts of a mixture consisting of 40 parts of a salt from1.5-dihydroxynaphthalene and l-amino-5-hydroxynaphthalene with 60 partsof Turkey red oil are dissolved in 1000 parts of water and the solutionis mixed with 20 parts of a hydrogen peroxide solution of 3 per cent.strength. A white lambskin mordanted with a chromium salt is dyed inthis bath at room temperature a dull red-brown in the course of 3 hours.

Example 20.--2 parts of a mixture consisting of 40 parts of a salt from1.6-dihyroxynaphthalene and 1-amino-5-hydroxynaphthalene with 60 partsof Turkey red oil are dissolved in 1000 parts of water and to thesolution are added 20 parts of a hydrogen peroxide solution of 3 percent. strength. A white rabbits skin, mordanted with a chromium salt isdyed in this bath at room temperature a bluish dark brown, in the courseof 3 hours.

Example 21.40 parts of a salt from l-amino- 5-hydroxynaphthalene andpara-aminodiphenylamine are mixed with 60 parts of a wetting agent madeas described in German Specification 3N0.

552,328 (Example 4). 2 parts of this mixture, are dissolved in 1000parts of water and to the solution are added 20 parts of a hydrogenperoxide solution of 3 per cent. strength. A white rabbit's skinmordanted with an iron salt is dyed in this bath at 30 C. a marine bluein the course of 3 hours.

Example 22.- parts of a mixture consisting oi 2.4 parts of the salt from1.5-dihydroxynaphthalene and 4-aminodiphenylamine, 1.28 parts of thesalt from 1.5-dihydroxynaphthalene and 1- methyl-2.4'-diaminobenzene,0.32 part of the salt from 1.6-dihydr0xynaphthalene and4-dimethylamino-2-amino-l-nitrobenzene and 6 parts of a dispersingagent; consisting of sulfonated solar oil, are dissolved in 1000 partsof water. The solution is mixed with 1000 parts 'of a hydrogen peroxidesolution. A lambskin mordanted with a chromium salt is dyed in this bathfull greenish black shades, the flesh side being blue.

Example 23.10 parts of a mixture consisting of 1.33 parts of the saltfrom 1.5-dihydroxynaphthalene and 4-aminodiphenylamine, 1.33 parts ofthe salt from 2.6-dihydroxynaphthalene and 4-amino-l-dimethylaminobenzene, 1.33 parts of the salt from1.5-dihydroxynaphthalene and 1.3-diaminobenzene and 6 parts of Turkeyred oil are dissolved in 1000 parts of water and the solution is mixedwith a hydrogen peroxide solution of 3 per cent. strength. An Indianlambskin treated with a chromium mordant, is dyed in this bath a fullblue black, the flesh side being light blue.

It is obvious that my invention is not limited to the foregoing examplesor to the specific details given therein. I have given a great number ofexamples in order to illustrate the performance of the new dyeing methodwith characteristic representants of the different groups of salts.However, numerous other embodiments are poosible, for instance, whenusing the derivatives and substitution products of the acid or basicconstituents of the salts.

, In a similar manner the dispersing agents mentioned in Examples 9 to23 may be substituted by other capillaractive compounds. Besides theproducts of this kind mentioned in the examples, I may use, forinstance, for the said purpose as mentioned above, sulfonated alkylnaphthalenes, aliphatic alcohol sulfonates, condensation products ofcresol sulfonic acids or hydroxynaphthalene sulfonic acids withformaldehyde, esters of saturated or unsaturated fatty acids withpolyglycol ethers or polyglycerines, sulfite cellulose waste liquor, andso on.

These possibilities are likewise indicated hi my specification and Icontemplate as included within my invention all such modifications andequivalents as fall within the scope of the appended claims.

What I claim is:

1. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent and a salt of the general formulawherein R is a member of the group consisting of hydroxynaphthyl,halogenonaphthyl, nitrohydroxynaphthyl, aminonaphthyl,aminohydroxynaphthyl, halogenohydroxynaphthyl andhalogenoaininonaphthyl, and R is an amino compound: of the groupconsisting. of aminobenzenes andi tt-minonaphthalenes. Q

2. Ihe process of dyeing pelts, furs, feathers anti materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent and a salt of the general formulaon-nm-iz' formula o H-HzNQ R I N\ y eral formula wherein R and R aremembers of the group consisting of hydrogen, alkyl, aryl, y is a memberof the group consisting of' hydrogen, alkyl, alkoxy, halogen and N02,and z is a member of the group consisting of OH and NH:.

4. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent and a salt of the genon-mN- i Nwherein R and R are members of the group consisting of hydrogen, alkyl,aryl, y is a member of the group consisting of hydrogen, alkyl, alkoxy,halogen and N02, and :r is a member of the group consisting of H andNH2.

5. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent and a salt of the general formula OH-HiN- R wherein R means an amino compound of the group consisting ofaminobenzenes and aminonaphthalenes and a: is a member of the groupconsisting of OH and NH2.

6. The process of dyeing pelts, furs, feathers and materialsmanufactured from thes products, which comprises treating them in a bathcontaining an oxidizing agent and a salt of the general formula OH-HaN-Rwherein R means an amino compound of the group consistingofaminobenzenes and aminonaphthalenes and a: is a member of the groupconsisting of OH and NH2.

'7. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products,

which comprises treating them in a bath containing an oxidizing agentand a salt of the general formula wherein R means an amino compound ofthe group consisting of aminobenzenes and aminonaphthalenes.

8. The process of dyeing pelts, furs, feathers and materialsmanufactured from these prodnote. which comprises treating them in abath containing an oxidizing agent and a salt of the general formulawherein R and R are members of the group consisting of hydrogen, alkyl,phenyl, alkoxyphenyl, aminophenyl, and y is a member of the groupconsisting of hydrogen, alkyl, alkoxy, halogen, N02.

9."I'he process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent and a salt of the general formulaOH-HaN wherein 1! is a member of the group consisting of hydrogen,alkyl, alkoxy, halogen, N02.

I 11. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent and a salt of the general formulaOBI-Ha y NH:

wherein y is a member of the group consisting of hydrogen, alkyl,alkoxy, halogen, N02.

12. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abathcontaining an oxidizing agent and a salt of the formula OH-BINQCIL13. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treatingthem in a bathcontaining anoxidizing agent and a salt of the formula DEMO-NR 14. Theprocess of dyeing pelts, furs, feathers and materials manufactured fromthese products, which comprises treating them in a bath containing anoxidizing agent and a salt of the formula C H: Oil-ENG 15. The processof dyeing pelts, fursffeathers and materials manufactured from theseproducts, which comprises treating them in a bath containing anoxidizing agent, a dispersing agent, and a salt of the general formulaR-OH-HaN-R' wherein R is an amino compound of the group consisting ofaminobenzenes and aminonaphthalenes and a: is a member of the groupconsisting of 0H and NI-Iz.

1'7. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products which comprises treating them in a bathcontaining an oxidizing agent, a dispersing agent, and a salt of *thegeneral formula wherein R and R are members of the group consisting ofhydrogen, alkyl, aryl, y is a member of the group consisting ofhydrogen, alkyl, alkoxy, halogen and NO: and a: is a member of the groupconsisting of OH and NH:.

18. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products.

halogenohydroxynaphthyi and which comprises treating them in a bathcontaining an oxidizing agent, a dispersing agent, and a salt of thegeneral formula wherein R and R are members of the group consisting ofhydrogen, alkyl, aryl, u is a member ofthe group consisting of hydrogen,alkyl, alkoxy. halogen and N02, and a: is a member of the groupconsisting of OH and NH2. I

19. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent, a dispersing agent, and a salt ofthe general formula 0 H- HIN- R wherein It means an amino compound ofthe group consisting of aminobenzenes and aminon'aphthalenes and it is amember of the group consisting of OH and NH2.

- 20, The process of dyeing pelts, furs, feathers and materialsmanufactured from these products,

which comprises treating them in a bath containing an oxidizing agent, adispersing agent, and a salt of the general formula wherein It means anamino compound of the group consisting of aminobenzenes andaminonaphthalenes and a: is ,a member of the group consisting of OH andNH2.

21. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in a'bath containing an oxidizing agent, a dispersing agent, and a salt ofthe general formula wherein It means an amino compound of the groupconsisting of aminobenzenes and aminonaphthalenes.

22. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent, a dispersing agent, and a salt ofthe general formula OH-HsN-Q R I y wherein R and R are members of thegroup consisting of hydrogen, alkyl, phenyl, alkoxyphenyl,

aminophenyl, and y is a member of the group.

consisting of hydrogen, alkyl, alkoxy, halogen, N02.

23. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent, a dispersing agent, and a salt ofthe general formula wherein y is a member of the group consisting ofhydrogen, alkyl, alkoxy, halogen, N02.

25. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent, a dispersing agent, and a salt ofthe general formula y NH:

wherein y is a member of the group consisting of hydrogen, alkyl,alkoxy, halogen, N02.

26. The process of dyeing pelts, furs, feathers and materialsmanufactured from these products, which comprises treating them in abath containing an oxidizing agent, a dispersing agent, and a salt ofthe formula or asm-Q0113 27. The process of dyeing pelts, furs, feathersand materials manufactured from these products, which comprises treatingthem in a bath containing an oxidizing agent, a dispersing agent, and asalt of the formula 28. The process of dyeing pelts, furs, feathers andmaterials manufactured from these products, which comprises treatingthem in a bath con-. taining an oxidizing agent, a dispersing agent, anda salt of the formula CHI ERICH LEHMANN.

